4-Cyano-4'-hydroxybiphenyl

Base Information

• Chemical Name: 4-Cyano-4'-hydroxybiphenyl
• CAS No.: 19812-93-2
• Molecular Formula: C13H9NO
• Molecular Weight: 195.221
• Hs Code.: 2926 90 70
• European Community (EC) Number: 427-840-4,623-191-8
• DSSTox Substance ID: DTXSID20941643
• Nikkaji Number: J86.507I
• Wikidata: Q72483372
• ChEMBL ID: CHEMBL114523
• Mol file: 19812-93-2.mol

Synonyms:19812-93-2;4-Cyano-4'-hydroxybiphenyl;4'-Hydroxy-4-biphenylcarbonitrile;4-(4-Hydroxyphenyl)benzonitrile;4-(4-Cyanophenyl)phenol;4'-Hydroxybiphenyl-4-carbonitrile;4'-Cyano-4-hydroxybiphenyl;4'-Hydroxy-[1,1'-biphenyl]-4-carbonitrile;4'-Hydroxy-biphenyl-4-carbonitrile;MFCD00059625;[1,1'-Biphenyl]-4-carbonitrile, 4'-hydroxy-;4'-Cyano-4-biphenylol;4'-hydroxy-4-cyanobiphenyl;CHEMBL114523;4/'-Hydroxy-4-biphenylcarbonitrile;4-CYANO-4'-HYDROXY-BIPHENYL;4'-Hydroxy-1,1'-biphenyl-4-carbonitrile;4'-Hydroxy[1,1'-biphenyl]-4-carbonitrile;4'-cyanobiphenyl-4-ol;4-(4'-cyanophenyl)phenol;4-Hydroxy-4'-cyanodiphenyl;Oprea1_683631;SCHEMBL83161;4'-cyano-4-hydroxy-biphenyl;4-Cyano-4/'-hydroxybiphenyl;IFLab1_000760;DTXSID20941643;4-hydroxy-4'-biphenylcarbonitrile;4`-Hydroxy-4-biphenylcarbonitrile;HMS1414C12;4'-hydroxy-4-biphenyl carbonitrile;4*-Hydroxy-biphenyl-4-carbonitrile;4-HYDROXY-4'-CYANOBIPHENYL;AMY25210;STR07142;4''-Hydroxy-biphenyl-4-carbonitrile;BDBM50121943;STK090858;4'-hydroxy-(4-biphenyl carbonitrile);AKOS001115836;AC-4951;CS-W002275;PS-8284;4'-Hydroxy-4-biphenylcarbonitrile, 97%;BP-20213;SY014463;4'-Hydroxy-[1,1-biphenyl]-4-carbonitrile;BB 0221180;FT-0618290;H0523;EN300-18398;4'-Hydroxy[1,1'-biphenyl]-4-carbonitrile #;A24066;SR-01000388889;Q-200463;SR-01000388889-1;Z57169647;4 inverted exclamation mark -Hydroxy-4-biphenylcarbonitrile

Chemical Property of 4-Cyano-4'-hydroxybiphenyl

Chemical Property:

• Appearance/Colour: light yellow to beige crystalline powder
• Vapor Pressure: 0.022 hPa (20 °C)
• Melting Point: 192-199 °C
• Refractive Index: 1.6060 (estimate)
• Boiling Point: 379.8 °C at 760 mmHg
• PKA: 9.43±0.26(Predicted)
• Flash Point: 183.5 °C
• PSA: 44.02000
• Density: 1.24 g/cm³
• LogP: 2.93088
• Storage Temp.: Room temperature.
• Solubility.: 12.7g/l no data available
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 195.068413911
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98% ^*data from raw suppliers

4''-Hydroxy-4-biphenylcarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22-36/37-9-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#N)C2=CC=C(C=C2)O
• Uses: Intermediates of Liquid Crystals

Technology Process of 4-Cyano-4'-hydroxybiphenyl

There total 55 articles about 4-Cyano-4'-hydroxybiphenyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-Cyanochlorobenzene (623-03-0) + (p-hydroxyphenyl)boronic acid (71597-85-8) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Guidance literature:

With potassium phosphate; catacxium A; palladium diacetate; In toluene; at 100 ℃; for 20h;

DOI:10.1055/s-2004-822313

Reference yield: 98.0%

4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-carbonitrile (406482-72-2) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Guidance literature:

With potassium phosphate; potassium peroxymonosulfate sulfate; In tetrahydrofuran; water; at 25 ℃; for 1h;

DOI:10.1021/jacs.0c06370

Reference yield: 91.0%

4-bromobenzenecarbonitrile (623-00-7) + 4-tert-butyl-dimethylsilyloxyphenylboronic acid anhydride (123088-32-4) → 4-Cyano-4'-hydroxybiphenyl (19812-93-2)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; at 95 ℃;

DOI:10.1016/S0968-0896(03)00303-1

upstream raw materials:

4-Cyanochlorobenzene

4-bromo-phenol

sodium phenoxide

4-amino-4'-cyanobiphenyl

Downstream raw materials:

4-cyano-4'-propyloxybiphenyl

4'-butoxybiphenyl-4-carbonitrile

Refernces

• 1、 Harloff, Joerg,Karsch, Markus,Lund, Henrik,Schulz, Axel,Villinger, Alexander. "Coordination networks based on nitrile-functionalized borate anions". . p. 1330 - 1341. Retrieved 2014.
• 2、 Hu, Rui,Li, Xinmin,Ren, Changyue,Yuan, Zeli,Zhang, Hang,Zhang, Tingting. "A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls". supporting information. p. 4748 - 4753. Retrieved 2020/08/17.
• 3、 Sang, Yali,Han, Sheng,Han, Shuwen,Pannecouque, Christophe,De Clercq, Erik,Zhuang, Chunlin,Chen, Fener. "Follow on-based optimization of the biphenyl-DAPYs as HIV-1 nonnucleoside reverse transcriptase inhibitors against the wild-type and mutant strains". . . Retrieved 2019/05/21.